Hydrochloric Acid → HCID 15027916, compound

HRID 1974472Notes

Reaction equation

HRID 1974472 reaction equation
Cl[CH:2]1[C:7](=[O:8])[NH:6][C:5]2[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=2[S:3]1.[F:13][C:14]1[CH:27]=[CH:26][C:17]([C:18]([CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[O:19])=[CH:16][CH:15]=1.C(N(CC)CC)C.Cl>C1(C)C=CC=CC=1.O>[F:13][C:14]1[CH:15]=[CH:16][C:17]([C:18]([CH:20]2[CH2:25][CH2:24][N:23]([CH:2]3[C:7](=[O:8])[NH:6][C:5]4[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=4[S:3]3)[CH2:22][CH2:21]2)=[O:19])=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 27244404-(4-Fluorobenzoyl)piperidineHCID 122185992H-1,4-Benzothiazin-3(4H)-one, 2-chloro-

Product 1

HCID 15027916HCID 15027916, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

7 g (=0.035 m) of 2-chloro-2H-1,4-benzothiazine-3(4H)-one, 7.25 g (=0.035 m) of 4-(4-fluorobenzoyl)-piperidine and 7.1 g of triethylamine in 200 ml of toluene were heated at reflux for 4 hours with stirring. The reaction mixture was worked up by cooling it and then adding 200 ml of toluene and 200 ml of water. The pH of the mixture was adjusted to pH 7 by adding 0.1N hydrochloric acid solution. The organic phase was separated, washed with 200 ml of water, and the solvent was distilled off. The title compound was recovered from the remaining oily residue by fractional column chromatography, crystallized from ethyl acetate, and recrystallized in an ethanol/diethyl ether mixture. 1.95 g of 2-[4-(4-fluorobenzoyl)-piperidin-1-yl]-2H-1,4-benzothiazine-3(4H)-one were obtained as a colorless crystalline powder having a melting point of 218° C.

Workup

  1. temperatureat reflux for 4 hours
  2. temperatureby cooling it
  3. customThe organic phase was separated
  4. washwashed with 200 ml of water
  5. distillationthe solvent was distilled off
  6. customThe title compound was recovered from the remaining oily residue by fractional column chromatography
  7. customcrystallized from ethyl acetate
  8. customrecrystallized in an ethanol/diethyl ether mixture

Sources & evidence

ORD record
ord-915c6333968c49bba312969d6ee65f1c
Source dataset
uspto-grants-1994_02
Patent number
US05283243

Reaction notes

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